Teasing, a common form of communication that involves ambiguity, is rendered more ambiguous through text messaging as the communicative markers that signal intent are restricted compared to face-to-face interaction. Although texting makes the ambiguity of teasing more prominent, nevertheless, there are elements of communication through texting that impact the interpretation of teasing texts, including message features (Study 1: the “lol” initialism and the “winking face with tongue” emoji), social context (Study 2: the sender–receiver relationship), and an individual’s rejection sensitivity (Study 1 and Study 2). In Study 1, the effects of message features were examined using a Latin square design with a sample of N = 490 undergraduate student participants. In Study 2, the effects of social context were examined using a classic counterbalancing design with a sample of N = 394 undergraduate student participants. The use of emoji and closer relationships resulted in more positive ratings of teasing messages, but the “lol” initialism did not contribute to more positive ratings of teasing. Across both studies, rejection sensitivity was related to more negative ratings of ambiguous text messages.